Diisopropylethylamine → 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-N-(1-phenylcyclopropyl)benzamide

HRID 44074Notes

Reaction equation

HRID 44074 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[C:35]1([C:41]2([NH2:44])[CH2:43][CH2:42]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Br:45][C:46]1[C:54]2[C:49](=[N:50][CH:51]=[C:52]([C:55]3[CH:56]=[C:57]([CH:61]=[CH:62][CH:63]=3)[C:58](O)=[O:59])[CH:53]=2)[O:48][C:47]=1[C:64]1[CH:69]=[CH:68][C:67]([F:70])=[CH:66][CH:65]=1>CN(C=O)C.CCOC(C)=O>[Br:45][C:46]1[C:54]2[C:49](=[N:50][CH:51]=[C:52]([C:55]3[CH:56]=[C:57]([CH:61]=[CH:62][CH:63]=3)[C:58]([NH:44][C:41]3([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:43][CH2:42]3)=[O:59])[CH:53]=2)[O:48][C:47]=1[C:64]1[CH:69]=[CH:68][C:67]([F:70])=[CH:66][CH:65]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1945481-PhenylcyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592336883-(3-Bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)benzoic acid

Product 1

HCID 672180313-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-N-(1-phenylcyclopropyl)benzamideYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIEA (286 μL, 1.64 mmol) was added to a stirring solution of HATU (311 mg, 0.819 mmol), 1-phenylcyclopropanamine hydrochloride (111 mg, 0.655 mmol), and 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)benzoic acid (225 mg, 0.546 mmol) in DMF (6 mL) at room temperature. It was allowed to stir for 1 hour. The mixture was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-N-(1-phenylcyclopropyl)benzamide (180 mg, 0.341 mmol, 63% yield) consistent by LCMS. LC-MS retention time: 1.89 min; m/z (MH+): 529. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. washwashed with 1M HCl
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b56e74acf593435ba0daa09a6cc629c8
Source dataset
uspto-grants-2013_09
Patent number
US08536338B2

Reaction notes

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